3-Nitrobenzenesulfonyl chloride → HCID 20035222, compound

Participants

Reaction Steps

A solution of 2-dimethylaminoethylamine (2.2 ml, 20 mmol) in tetrahydrofuran (25 ml) was added over 30 minutes to a stirred solution of 3-nitrobenzenesulfonyl chloride (2.2 g, 10 mmol) in tetrahydrofuran (50 ml) cooled in an ice bath. After addition was complete, the reaction mixture was stirred in the ice bath for 30 minutes, then at 20°-25° for 20 hours. Solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The ethyl acetate extract was washed with a saturated aqueous solution of sodium chloride, dried (Na2SO4), filtered and concentrated. The residue was flash chromatographed on silica gel and eluted with 5% methanol-95% chloroform to give pure base. Further purification was effected by conversion to the HCl salt (1.75 g), m.p. 174.0°-76.0° C.

Provenance & Evidence